It is common for women who are breastfeeding to express breast milk for the purpose of storing the milk to feed an infant at other times, such as when she is unable or unavailable to breast-feed the infant. Breast pumps are typically used to express the milk from a breast by generating intermittent suction or vacuum at a nipple to simulate a feeding or suckling infant. To provide the proper suction, breast pumps usually include a funnel or funnel-shaped cup or breast shield that is sized to be positioned over the nipple area of the breast. The breast pump then generates the intermittent suction in the funnel, such as via an electric motor or other vacuum device, to express the milk and draw it into a collection container attached to the funnel. However, to ensure that a seal is formed between the funnel and the breast for the intermittent suction to properly express milk, the woman typically holds the funnel tightly against the nipple area. This can be challenging when multi-tasking or pumping both breasts simultaneously.